Boston Red Sox

By Tony Massarotti, 98.5 The Sports Hub

Suddenly, it seems, the Red Sox are intent on signing Chris Sale. And true to form, I feel like it’s a mistake.

OK, so maybe I’m reading into all of this too much. Or maybe I’m not. But when asked about Sale on Monday during his annual State of the Sox address with fellow owner Tom Werner, Red Sox principal owner John Henry strongly suggested that the Sox regarded Sale as an outlier, the kind of 30-year-old pitcher to whom typical aging concerns do not apply. A reporter then suggested that the same could have been said of Jon Lester, who had just turned 30 in 2014 and was entering the final year of his contract when the Red Sox all but gave him his AARP card.

We all know how that turned out.

“I think we blew the [Lester] signing in spring training,” Henry said.

Wait … what???!!!

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Fine, so five years after the fact, the Red Sox have admitted that they blew it with Lester. But that’s not the story here. The story is that, at the time, Red Sox ownership (read: Henry) preached the dangers of signing 30-year-old players to exorbitant contracts. Theoretically, this made Lester a bad investment, at least based on what Henry told Bloomberg BusinessWeek.

“To me, the most important thing this study shows is that virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30,” Henry said at the time. “Yet teams continue to extravagantly overpay for players above the age of 30.”

So now we know why then-president Larry Lucchino and the Red Sox opened negotiations with Lester by proposing a four-year, $70-million offer that the pitcher ultimately took as an insult. We took it as a halfhearted, public relations ploy to make it look like the Red Sox wanted Lester when they really didn’t.

But now here we are, five years later, and Henry is suggesting something altogether different. He’s telling us that the Red Sox wanted Lester – but that they (read: Lucchino) blew it. And all of that suggests the team is now willing to pony up for a 30-year-old pitcher similarly entering the final year of his contract.

Apples to apples, right?


Oct 28, 2018; Los Angeles, CA, USA; Boston Red Sox pitcher Chris Sale (41) pitches in the ninth inning against the Los Angeles Dodgers in game five of the 2018 World Series at Dodger Stadium. Mandatory Credit: Gary A. Vasquez-USA TODAY Sports

Here’s the obvious difference: unlike Sale, Lester had no durability issues – and he certainly didn’t effectively miss three months in the final weeks before his contract year. Maybe this is why Henry went out of his way to say that Sale is “healthy” and that he “hasn’t had any significant shoulder issues.” In the process, he told us more about Sale’s injury late last year than anybody with the Red Sox ever did at the time (or since).

So, does that mean the Red Sox should just give Sale whatever he wants? Hardly. But you can bet president of baseball operations Dave Dombrowski is angling for it. Dombrowski has a history of giving out big contracts to players – Miguel Cabrera and Justin Verlander in Detroit, David Price in Boston, and there are others – so he’s not gun shy. More importantly, the Red Sox don’t have anyone in their minor league system even remotely ready to be Sale’s replacement, which means the Red Sox have no leverage. Maybe they’re even desperate.

And that, as always, has the makings of a disaster.

You can hear Tony Massarotti weekdays from 2-6 p.m. EST on the Felger & Massarotti program. Follow him on Twitter @TonyMassarotti.